Chloride → HCID 54326320, compound

HRID 1492908Notes

Reaction equation

[Cl:1][CH:2]([P:17](=[O:30])([O:24][CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[O:18][CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[P:3](=[O:16])([O:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[O:4][CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.[Cl-].[Br:32][O-].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:32][C:2]([Cl:1])([P:3](=[O:16])([O:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[O:4][CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)[P:17](=[O:30])([O:24][CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[O:18][CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 10 °C

Procedure

4.8 g (0.01 moles) of tetracyclopentyl (monochloromethylene)bisphosphonate (31P-NMR (CDCl3): δ 12.44 ppm, 2JPH =17.7 Hz) are dissolved in 20 ml of carbontetrachloride and 0.55 g of bensyltriethylammonium chloride and 20 ml of a 10% sodium hypobromite solution are added while cooling and stirring at about 10° C. The mixture is stirred vigorously for 30 min at about 10° C. and the organic phase is separated, washed with water, dried (Na2SO4) and filtered. The filtrate is evaporated in a vacuum, whereby about 5.0 g (90% of the theor.) of tetracyclopentyl (bromochloromethylene)bisphosphonate (31P-NMR (CDCl3): δ 7.68 ppm) is obtained as a colourless oil at a concentration of >80%.

Workup

temperaturewhile cooling
stirringThe mixture is stirred vigorously for 30 min at about 10° C.
customthe organic phase is separated
washwashed with water
dry with materialdried (Na2SO4)
filtrationfiltered
customThe filtrate is evaporated in a vacuum, whereby about 5.0 g (90% of the theor

Sources & evidence

ORD record: ord-eced28fe334a49ea9a689b9c99457bae
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05376649

Reaction notes

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